Int.J.Curr.Microbiol.App.Sci (2015) 4(12): 630-639
ISSN: 2319-7706 Volume 4 Number 12 (2015) pp. 630-639
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Original Research Article
Preparation of Dioxadiazole from Aryl Acid Hydrazide with Adipoyl Chloride
Intesar.O. Al Tamimi*, Muna.I. Al Heeti and Jaafar.Z.Aziz
Department of Chemistry College of Science University of Baghdad, Iraq
*Corresponding author
ABSTRACT
Keywords
Dioxadiazole,
Aryl Acid,
Hydrazide,
Adipoyl
Chloride,
triethylamine
The present work involved preparation of diaromatic heterocyclic
compounds The first step involved preparation of 2-substitution butyl
benzoate (1-4), second step preparation of 2-substitution benz acid
hydrazide (5-8),then preparation of dioxadiazole (9-12) from the reaction of
two molecules of 2-substitution benz acid hydrazide with adipoyl chloride in
the present triethylamine as catalyst. All the prepared compounds in this
work were characterized by melting points with other physical properties,
infrared (FTIR) and 1H-NMR, 13C-NMR spectra Screening microbial
activity of the preparation dioxadiazole compounds were evolution against
two types of (Gram positive).
Introduction
reported the use of diethylamino difluoro
sulfinium tetrafluoroborate ([Et2NSF2]
BF4), XtalFluor-E, as a new cyclo
dehydration agent for the preparation of
1,3,4-oxadiazoles from 1,2-diacyl hydrazine.
Oxadiazole rings have been introduced into
drug discovery oxadiazoles are having a
large impact on multiple drug discovery
programs across a variety of disease areas,
including
diabetes,
obesity(14),
inflammation (15), cancer (16), and
infection (17).
Oxadiazole is a five-number heterocyclic
aromatic chemical compound having two
carbons, two nitrogen, and one oxygen
atoms and two double bonds having general
formula C2H2N2O. There are four possible
isomers of oxadiazole (1, 2, 3, 4) depending
on the position of nitrogen atom in the ring.
The1,3,4-oxadiazole undergoes number of
reactions
including
electrophillic
substitution,
nucleophilic
substitution,
thermal and photochemical(1-11). Guin and
co-workers (12) reported a direct route to
both symmetrical and unsymmetrical 2,5disubstituted-1,3,4- oxadiazoles by means of
an imine C-H functionalization of Narylidenearoylhydrazide using Cu()2 as
catalyst. Pouliot and co-workers (13)
1,3,4-oxadiazole used in medicine and
agriculture, in the production of polymers,
laser dyes, photographic materials(18).
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Int.J.Curr.Microbiol.App.Sci (2015) 4(12): 630-639
Experimental
General Procedure for Synthesis for
Dioxadiazole (20) (9-12)
The melting points were determined on a
Kofler Block apparatus and are uncorrected.
In a 100 ml round bottomed flask dissolve
(0.00105mol) of aromatic acid hydrazide (912) in benzene. Place (1ml) of trimethyl
amine and(0.2ml) of adipoyl chloride to
round bottom flask,the mixture was refluxed
for(1hrs).cool the mixture at room
temperature, physical properties shown in
table (3).
Infrared spectra were recorded in 400 - 4000
cm-1 region by a Specord FT-IR on
SHIMADZU FTIR-8400.
spectrometer using KBr tablet. 1HNMR,13C-NMR Spectra were measured on
ambient Broker DT-400 MHz,Iran.
Results and Discussion
spectrometer in deuterated DMSO, ] The
magnetic stirrer and the other necessary
laboratory equipment used. All fine
chemicals and, reagents were purchased
froM,Aldrich chemical Co. U.S.A. and
microbial activity were done in the plant
biology department laboratories.
A four oxadiazole products (9,10,11,12)
were obtained by series reactions starting
with preparation of ester then preparation of
benz acid hydrazaid ended with di
oxadiazoles in the chosen solvent, in normal
conditions. All products are stable oily
compounds, rather insoluble in common
solvents, with high melting points. (Table
3).
General Procedure for Synthesis of Esters
(19)(1-4)
In beaker dissolve the different aromatic
carboxylic acids with benzene. In a 100 ml
round bottomed flask place (0.025mol) of
aromatic carboxylic acid and (1.5ml) of
butanol and added (3-4 drops) of
concentrated sulphuric acid. Fit the flask
with a reflux condenser for (2hrs). Cool the
mixture at room temperature, physical
properties shown in table (1).
General Procedure for Synthesis of Benz
Acid Hydrazide (19) (5-8)
In a 100ml round bottomed flask place
(0.012mol) of esters and (0.012mol) of
hydrazine hydrate and added (10ml) of
ethanol.fit the mixture refluxed for (2hrs).
Cool the mixture at room temperature, the
color precipitate was filtered, dried and
recrystallization with (O-xylene), physical
properties shown in table (2).
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Int.J.Curr.Microbiol.App.Sci (2015) 4(12): 630-639
Table.1 Physical Properties of Prepared Ester Compounds
Table.2 Physical Properties of Prepared 2-Substituted Benz Acid Hydrazide Compounds
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Int.J.Curr.Microbiol.App.Sci (2015) 4(12): 630-639
Table.3 Physical Properties of Prepared Dioxadiazole Compounds
Table.4 FTIR Spectrum of Dioxadiazole Compound
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Table.5.Antimicrobial Activity of Oxadiazole Compounds
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Int.J.Curr.Microbiol.App.Sci (2015) 4(12): 630-639
Fig.3 FTIR Spectrum of Compound( 6)
Fig.4 FTIR Spectrum of Compound( 7)
Fig.5 FTIR Spectrum of Compound( 9 )
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Int.J.Curr.Microbiol.App.Sci (2015) 4(12): 630-639
Fig.6 FTIR Spectrum of Compound (10)
Fig.7 1H -NMR Spectrum of Compound (6)
Fig.8 13C-NMR Spectrum of Compound (6)
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Int.J.Curr.Microbiol.App.Sci (2015) 4(12): 630-639
Fig.9 1H -NMR Spectrum of Compound (11)
Fig.10 13C-NMR Spectrum of Compound (11)
FTIR Spectra for the compounds ester (1-4)
were show appearance absorption bands of
(C=O )of ester at(1734,1743,1750,1742 cm1), Fig(1,2), While FTIR spectra of acid
hydrazaid compounds (5-8) showed
disappearance of the absorption bands(C=O)
ester
with
appearance
absorption
bands(C=O) of amide at (1654- 1689)cm-1
as well as distinguish band at the region
(3100-3400) cm -1 of (NH) and (NH2),
hydrazaide Fig (3,4).While FTIR of
compounds (9 12 ) showed disappearance
of the absorption bands(C=O) and
absorption bands of (NH2) and (NH),
hydrazaide with appearance of absorption
bands of(C-N),(C=N) and (CH2),Fig (5,6).
1H-NMR spectra of oxa diazoles comp. (912), indicate disappearance of proton signals
for the( amino group hydrazide) of all
compounds)at (9,5) ppm, and appearance
of a protons of methylene (CH2) at (3.4)
ppm and protons of (aromatic ring) at(7-8)
ppm for all prepared compounds. Fig(7,9).
Antibacterial Activity by Well Diffusion
Method
Pertiplates containing (20 ml) muller Hiuton
medium were seeded with (24hr) culture of
bacterial strains, well were cut and
20micromill liter of the plant extracts
(namely aqueous, methanol and chloroform
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Int.J.Curr.Microbiol.App.Sci (2015) 4(12): 630-639
extracts) were added, the plates were then
incubated
at
370C
for
(24hr),the
antibacterial activity was assayed by
measuring the diameter of the inhibition
zone
formed
around
the
well.
chloramphenicol dis was used as appositive
control
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